CA3048552A1 - Chemical compounds for coating of nanostructures - Google Patents
Chemical compounds for coating of nanostructures Download PDFInfo
- Publication number
- CA3048552A1 CA3048552A1 CA3048552A CA3048552A CA3048552A1 CA 3048552 A1 CA3048552 A1 CA 3048552A1 CA 3048552 A CA3048552 A CA 3048552A CA 3048552 A CA3048552 A CA 3048552A CA 3048552 A1 CA3048552 A1 CA 3048552A1
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- Prior art keywords
- core
- group
- compound
- nanostructure
- coated
- Prior art date
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- 239000002086 nanomaterial Substances 0.000 title claims abstract description 251
- 150000001875 compounds Chemical class 0.000 title claims abstract description 97
- 238000000576 coating method Methods 0.000 title description 77
- 239000011248 coating agent Substances 0.000 title description 73
- 239000000203 mixture Substances 0.000 claims abstract description 72
- 238000000034 method Methods 0.000 claims abstract description 65
- 229920001477 hydrophilic polymer Polymers 0.000 claims abstract description 57
- 125000003118 aryl group Chemical group 0.000 claims abstract description 49
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 41
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 29
- 238000004873 anchoring Methods 0.000 claims abstract description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 22
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims abstract description 16
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 15
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 15
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 239000001301 oxygen Substances 0.000 claims abstract description 14
- 239000011574 phosphorus Substances 0.000 claims abstract description 14
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 11
- 239000010703 silicon Substances 0.000 claims abstract description 11
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000011593 sulfur Substances 0.000 claims abstract description 9
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 7
- 239000004305 biphenyl Substances 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 54
- -1 gadolinium(III) ion Chemical class 0.000 claims description 36
- 238000003384 imaging method Methods 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 27
- 150000004756 silanes Chemical class 0.000 claims description 23
- 150000004663 bisphosphonates Chemical group 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 17
- 238000001959 radiotherapy Methods 0.000 claims description 17
- 238000002603 single-photon emission computed tomography Methods 0.000 claims description 14
- 239000002616 MRI contrast agent Substances 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 11
- 239000004202 carbamide Substances 0.000 claims description 9
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 claims description 8
- 239000003125 aqueous solvent Substances 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 62
- 239000000243 solution Substances 0.000 description 62
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- 230000015572 biosynthetic process Effects 0.000 description 40
- 238000003786 synthesis reaction Methods 0.000 description 40
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 32
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 32
- 239000003054 catalyst Substances 0.000 description 31
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 238000005160 1H NMR spectroscopy Methods 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000011572 manganese Substances 0.000 description 25
- 230000002194 synthesizing effect Effects 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 229920000642 polymer Polymers 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 19
- 229910052748 manganese Inorganic materials 0.000 description 19
- 239000002872 contrast media Substances 0.000 description 18
- 239000002243 precursor Substances 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 230000008901 benefit Effects 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
- 235000019198 oils Nutrition 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- 229920001223 polyethylene glycol Polymers 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 229910000077 silane Inorganic materials 0.000 description 15
- 238000006880 cross-coupling reaction Methods 0.000 description 14
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 14
- 230000005298 paramagnetic effect Effects 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 239000000654 additive Substances 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 12
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 11
- 229910052688 Gadolinium Inorganic materials 0.000 description 11
- 238000002474 experimental method Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 150000003058 platinum compounds Chemical class 0.000 description 11
- 230000002829 reductive effect Effects 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- 238000006619 Stille reaction Methods 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- OHSVLFRHMCKCQY-NJFSPNSNSA-N lutetium-177 Chemical compound [177Lu] OHSVLFRHMCKCQY-NJFSPNSNSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 239000002202 Polyethylene glycol Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229940093476 ethylene glycol Drugs 0.000 description 9
- 230000026030 halogenation Effects 0.000 description 9
- 238000005658 halogenation reaction Methods 0.000 description 9
- WUAPFZMCVAUBPE-IGMARMGPSA-N rhenium-186 Chemical compound [186Re] WUAPFZMCVAUBPE-IGMARMGPSA-N 0.000 description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 9
- UYEMGAFJOZZIFP-UHFFFAOYSA-N 3,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(O)=C1 UYEMGAFJOZZIFP-UHFFFAOYSA-N 0.000 description 8
- GYHNNYVSQQEPJS-OIOBTWANSA-N Gallium-67 Chemical compound [67Ga] GYHNNYVSQQEPJS-OIOBTWANSA-N 0.000 description 8
- 206010028980 Neoplasm Diseases 0.000 description 8
- 229910020667 PBr3 Inorganic materials 0.000 description 8
- IGLNJRXAVVLDKE-OIOBTWANSA-N Rubidium-82 Chemical compound [82Rb] IGLNJRXAVVLDKE-OIOBTWANSA-N 0.000 description 8
- 229940125666 actinium-225 Drugs 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 8
- RYGMFSIKBFXOCR-YPZZEJLDSA-N copper-62 Chemical compound [62Cu] RYGMFSIKBFXOCR-YPZZEJLDSA-N 0.000 description 8
- RYGMFSIKBFXOCR-IGMARMGPSA-N copper-64 Chemical compound [64Cu] RYGMFSIKBFXOCR-IGMARMGPSA-N 0.000 description 8
- RYGMFSIKBFXOCR-AKLPVKDBSA-N copper-67 Chemical compound [67Cu] RYGMFSIKBFXOCR-AKLPVKDBSA-N 0.000 description 8
- 238000003818 flash chromatography Methods 0.000 description 8
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 8
- 229910052736 halogen Inorganic materials 0.000 description 8
- 150000002367 halogens Chemical class 0.000 description 8
- 150000004678 hydrides Chemical class 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 8
- 238000002595 magnetic resonance imaging Methods 0.000 description 8
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 8
- HCWPIIXVSYCSAN-OIOBTWANSA-N radium-223 Chemical compound [223Ra] HCWPIIXVSYCSAN-OIOBTWANSA-N 0.000 description 8
- KZUNJOHGWZRPMI-AKLPVKDBSA-N samarium-153 Chemical compound [153Sm] KZUNJOHGWZRPMI-AKLPVKDBSA-N 0.000 description 8
- CIOAGBVUUVVLOB-OUBTZVSYSA-N strontium-89 Chemical compound [89Sr] CIOAGBVUUVVLOB-OUBTZVSYSA-N 0.000 description 8
- ZSLUVFAKFWKJRC-FTXFMUIASA-N thorium-227 Chemical compound [227Th] ZSLUVFAKFWKJRC-FTXFMUIASA-N 0.000 description 8
- GYHNNYVSQQEPJS-YPZZEJLDSA-N Gallium-68 Chemical compound [68Ga] GYHNNYVSQQEPJS-YPZZEJLDSA-N 0.000 description 7
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 7
- 230000001965 increasing effect Effects 0.000 description 7
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 7
- 239000012280 lithium aluminium hydride Substances 0.000 description 7
- 238000012636 positron electron tomography Methods 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- 229960005562 radium-223 Drugs 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- WUAPFZMCVAUBPE-NJFSPNSNSA-N 188Re Chemical compound [188Re] WUAPFZMCVAUBPE-NJFSPNSNSA-N 0.000 description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 6
- VWQVUPCCIRVNHF-OIOBTWANSA-N Yttrium-86 Chemical compound [86Y] VWQVUPCCIRVNHF-OIOBTWANSA-N 0.000 description 6
- VWQVUPCCIRVNHF-OUBTZVSYSA-N Yttrium-90 Chemical compound [90Y] VWQVUPCCIRVNHF-OUBTZVSYSA-N 0.000 description 6
- 238000005937 allylation reaction Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- KJZYNXUDTRRSPN-OUBTZVSYSA-N holmium-166 Chemical compound [166Ho] KJZYNXUDTRRSPN-OUBTZVSYSA-N 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- APFVFJFRJDLVQX-AHCXROLUSA-N indium-111 Chemical compound [111In] APFVFJFRJDLVQX-AHCXROLUSA-N 0.000 description 6
- 231100000053 low toxicity Toxicity 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 229910001437 manganese ion Inorganic materials 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- XGHFPTMUVIDZNF-UHFFFAOYSA-N methyl 2,6-dibromopyridine-4-carboxylate Chemical compound COC(=O)C1=CC(Br)=NC(Br)=C1 XGHFPTMUVIDZNF-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
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- 239000004810 polytetrafluoroethylene Substances 0.000 description 6
- 238000006886 vinylation reaction Methods 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 5
- 238000012879 PET imaging Methods 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- GKLVYJBZJHMRIY-OUBTZVSYSA-N Technetium-99 Chemical compound [99Tc] GKLVYJBZJHMRIY-OUBTZVSYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 5
- 239000011575 calcium Chemical class 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
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- 229930195733 hydrocarbon Natural products 0.000 description 5
- 238000001990 intravenous administration Methods 0.000 description 5
- WABPQHHGFIMREM-BKFZFHPZSA-N lead-212 Chemical compound [212Pb] WABPQHHGFIMREM-BKFZFHPZSA-N 0.000 description 5
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- 125000006239 protecting group Chemical group 0.000 description 5
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- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
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- QQINRWTZWGJFDB-YPZZEJLDSA-N actinium-225 Chemical compound [225Ac] QQINRWTZWGJFDB-YPZZEJLDSA-N 0.000 description 4
- 125000004423 acyloxy group Chemical group 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 4
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- RJOJUSXNYCILHH-UHFFFAOYSA-N gadolinium(3+) Chemical compound [Gd+3] RJOJUSXNYCILHH-UHFFFAOYSA-N 0.000 description 4
- 229940006110 gallium-67 Drugs 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
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- 229940006509 strontium-89 Drugs 0.000 description 4
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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- OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 3
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 3
- LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 3
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- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nanotechnology (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Radiology & Medical Imaging (AREA)
- Dispersion Chemistry (AREA)
- Physics & Mathematics (AREA)
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- Medical Informatics (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Biophysics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Silicon Polymers (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Paints Or Removers (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP17151653.7 | 2017-01-16 | ||
| EP17151653.7A EP3348560A1 (en) | 2017-01-16 | 2017-01-16 | Chemical compounds for coating of nanostructures |
| PCT/EP2018/050975 WO2018130713A1 (en) | 2017-01-16 | 2018-01-16 | Chemical compounds for coating of nanostructures |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA3048552A1 true CA3048552A1 (en) | 2018-07-19 |
Family
ID=57799639
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3048552A Pending CA3048552A1 (en) | 2017-01-16 | 2018-01-16 | Chemical compounds for coating of nanostructures |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US11401376B2 (ko) |
| EP (2) | EP3348560A1 (ko) |
| JP (1) | JP7078274B2 (ko) |
| KR (1) | KR102536477B1 (ko) |
| CN (1) | CN110191890B (ko) |
| AU (1) | AU2018208538B2 (ko) |
| BR (1) | BR112019014483B1 (ko) |
| CA (1) | CA3048552A1 (ko) |
| DK (1) | DK3568403T3 (ko) |
| ES (1) | ES2880228T3 (ko) |
| IL (1) | IL267895B2 (ko) |
| PL (1) | PL3568403T3 (ko) |
| RU (1) | RU2757904C2 (ko) |
| WO (1) | WO2018130713A1 (ko) |
| ZA (1) | ZA201904405B (ko) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7233912B2 (en) | 1997-08-26 | 2007-06-19 | Walker Digital, Llc | Method and apparatus for vending a combination of products |
| TWI644942B (zh) * | 2015-06-12 | 2018-12-21 | 日商大金工業股份有限公司 | 表面處理劑 |
| EP3838967A1 (en) * | 2019-12-16 | 2021-06-23 | Spago Nanomedical AB | Immobilization of phenolic compounds |
| CN114015036A (zh) * | 2021-11-01 | 2022-02-08 | 三棵树(上海)新材料研究有限公司 | 低粘度硅烷改性聚醚树脂及其制备方法 |
| EP4242250A1 (en) | 2022-03-08 | 2023-09-13 | Spago Nanomedical AB | Compounds for coating of nanostructures |
| EP4241792A1 (en) * | 2022-03-08 | 2023-09-13 | Spago Nanomedical AB | Nanostructures and applications thereof |
| EP4241765A1 (en) * | 2022-03-08 | 2023-09-13 | Spago Nanomedical AB | Globular nanostructures having an anchoring layer |
| EP4241793A1 (en) * | 2022-03-08 | 2023-09-13 | Spago Nanomedical AB | Globular nanostructures |
| CN116608891B (zh) * | 2023-07-20 | 2023-11-03 | 山东省科学院激光研究所 | 一种光纤f-p腔传感器及其制造方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6310243B1 (en) | 1994-09-23 | 2001-10-30 | Nycomed Imaging As | Iodinated x-ray contrast media |
| AU2006284565B2 (en) * | 2005-09-02 | 2013-05-30 | Visen Medical, Inc. | Biocompatible N, N-disubstituted sulfonamide-containing fluorescent dye labels |
| EP2272897B1 (en) * | 2008-03-10 | 2016-12-28 | The University of Tokyo | Copolymer including uncharged hydrophilic block and cationic polyamino acid block having lateral chain to which hydrophobic radical is partially introduced, and use of copolymer |
| KR20110075029A (ko) * | 2008-10-21 | 2011-07-05 | 엔즌 파마슈티칼스, 인코포레이티드 | 7-에틸-10-하이드록시캄토테신의 다중-암 고분자 컨쥬게이트로 신경모세포종의 치료 |
| KR101252063B1 (ko) * | 2011-08-25 | 2013-04-12 | 한국생산기술연구원 | 알콕시실릴기를 갖는 에폭시 화합물, 이의 제조 방법, 이를 포함하는 조성물과 경화물 및 이의 용도 |
| EP2572736A1 (en) | 2011-09-23 | 2013-03-27 | Spago Imaging AB | Nanostructures comprising manganese |
| WO2013137663A1 (ko) * | 2012-03-14 | 2013-09-19 | 한국생산기술연구원 | 알콕시실릴기를 갖는 에폭시 화합물, 이를 포함하는 조성물, 경화물, 이의 용도 및 알콕시실릴기를 갖는 에폭시 화합물의 제조방법 |
| EP2857436B1 (en) * | 2012-05-31 | 2019-10-09 | Kaneka Corporation | Polymer having terminal structure including plurality of reactive silicon groups, method for manufacturing same, and use for same |
| KR101520764B1 (ko) * | 2012-06-01 | 2015-05-15 | 한국생산기술연구원 | 알콕시실릴기를 갖는 에폭시 화합물, 무기입자를 포함하는 조성물, 경화물, 이의 용도 및 알콕시실릴기를 갖는 에폭시 화합물의 제조방법 |
| NZ705910A (en) * | 2012-10-12 | 2018-09-28 | Medimmune Ltd | Pyrrolobenzodiazepines and conjugates thereof |
| WO2014057120A1 (en) * | 2012-10-12 | 2014-04-17 | Adc Therapeutics Sàrl | Pyrrolobenzodiazepine-antibody conjugates |
| KR101755323B1 (ko) * | 2014-02-19 | 2017-07-20 | 한국생산기술연구원 | 신규한 에폭시 화합물, 이를 포함하는 혼합물, 조성물, 경화물, 이의 제조 방법, 및 이의 용도 |
| EP2923712A1 (en) | 2014-03-28 | 2015-09-30 | Spago Imaging AB | Nanostructures and applications thereof |
| CN104530417B (zh) * | 2014-10-01 | 2017-09-08 | 厦门赛诺邦格生物科技股份有限公司 | 一种多官能化h型聚乙二醇衍生物及其制备方法 |
| US11324827B2 (en) * | 2014-10-01 | 2022-05-10 | Xiamen Sinopeg Biotech Co., Ltd. | Multifunctionalized polyethylene glycol derivative and preparation method therefor |
| EP3464789B1 (en) * | 2016-06-07 | 2021-04-28 | Welltec A/S | Downhole operational tool |
-
2017
- 2017-01-16 EP EP17151653.7A patent/EP3348560A1/en not_active Withdrawn
-
2018
- 2018-01-16 CN CN201880007103.7A patent/CN110191890B/zh active Active
- 2018-01-16 JP JP2019537162A patent/JP7078274B2/ja active Active
- 2018-01-16 EP EP18700364.5A patent/EP3568403B1/en active Active
- 2018-01-16 IL IL267895A patent/IL267895B2/en unknown
- 2018-01-16 BR BR112019014483-8A patent/BR112019014483B1/pt active IP Right Grant
- 2018-01-16 US US16/477,995 patent/US11401376B2/en active Active
- 2018-01-16 PL PL18700364T patent/PL3568403T3/pl unknown
- 2018-01-16 DK DK18700364.5T patent/DK3568403T3/da active
- 2018-01-16 RU RU2019125812A patent/RU2757904C2/ru active
- 2018-01-16 KR KR1020197023903A patent/KR102536477B1/ko active IP Right Grant
- 2018-01-16 AU AU2018208538A patent/AU2018208538B2/en active Active
- 2018-01-16 ES ES18700364T patent/ES2880228T3/es active Active
- 2018-01-16 WO PCT/EP2018/050975 patent/WO2018130713A1/en active Application Filing
- 2018-01-16 CA CA3048552A patent/CA3048552A1/en active Pending
-
2019
- 2019-07-04 ZA ZA2019/04405A patent/ZA201904405B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20190352459A1 (en) | 2019-11-21 |
| AU2018208538B2 (en) | 2021-05-20 |
| BR112019014483A2 (pt) | 2020-02-11 |
| CN110191890B (zh) | 2022-11-15 |
| RU2757904C2 (ru) | 2021-10-22 |
| EP3568403B1 (en) | 2021-04-21 |
| PL3568403T3 (pl) | 2021-11-08 |
| KR20190104598A (ko) | 2019-09-10 |
| BR112019014483B1 (pt) | 2023-01-17 |
| ES2880228T3 (es) | 2021-11-24 |
| IL267895A (en) | 2019-09-26 |
| RU2019125812A (ru) | 2021-02-16 |
| RU2019125812A3 (ko) | 2021-05-12 |
| CN110191890A (zh) | 2019-08-30 |
| DK3568403T3 (da) | 2021-07-12 |
| WO2018130713A1 (en) | 2018-07-19 |
| EP3348560A1 (en) | 2018-07-18 |
| ZA201904405B (en) | 2022-09-28 |
| JP2020507559A (ja) | 2020-03-12 |
| KR102536477B1 (ko) | 2023-05-25 |
| AU2018208538A1 (en) | 2019-07-18 |
| JP7078274B2 (ja) | 2022-05-31 |
| IL267895B (en) | 2022-12-01 |
| EP3568403A1 (en) | 2019-11-20 |
| IL267895B2 (en) | 2023-04-01 |
| US11401376B2 (en) | 2022-08-02 |
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